CHM 112
GAGE
SPRING 2002
NAME _____________________________
DATE _____________________________
MID-TERM EXAM
1.
Write the name for each of the following compounds:
(24)
CH 3
H2
C
C
H3C
CH
H2C
Cl
O
CH 3
C
H2
C
Cl
CH 2
H2
C
H3C
H2
C
C
N
H
CH 3
C
H2
H3C
CH 2
O
C
H2
H
N-ethyl pentanamide
H3C
H2
C
C
C
H2
C
H2
4-cyclohexyl butanal
3, 7-dichloro-3, 6, 6-trimethyl decane
O
CH 3
H2
C
H3C
O
C
O
Br
C
CH 3
CH 3
H3C
C
H2
CH 3
H2
C
C
O
CH 3
3-chloro-4-heptanone
O
CH
CH
Cl
3-bromo benzoic acid
CH3
H2
C
C
OH
ethyl t-butyl ether
H3C
H2
C
H
H 3C
H2
C
C
C
C
H2
CH 3
CH 2
isopropyl methanoate
2. a.
H 3C
3-ethyl-4-methyl-3-heptene
A benzene ring has three double bonds. Can it undergo addition? Explain why or why
not.
(5)
Benzene will not undergo addition because the electrons in the double bonds are
“delocalized”. Since they do not reside between two specific carbons all the time, it is
harder to commandeer those electrons to use in making additional bonds on two adjacent
carbons.
b. Why would an acid or amine functional group on a compound be converted to the salt
form before being used in a medication?
(5)
The salt form of an acid or amine contains an ionically bonded region. These compounds
will be much more soluble in water because of stronger ion-dipole forces that form with
water rather than the dipole-dipole forces.
1
c.
3.
Which has a higher energy, a single carbon-carbon bond or a double carbon-carbon bond.
Explain your answer.
(5)
The C-C double bond will be higher energy because there is greater repulsion with two
pairs of electrons between two carbon nuclei than with one pair. This generates a higher
energy state to maintain the bond.
Write the full or condensed structural formula for each of the following compounds.
(24)
acetone
N-methyl-N-isopropyl aniline
4-ethyl toluene
CH 3
O
C
H3C
CH 3
CH3
N
CH
H3C
CH 3
CH 2
H 3C
pentyl heptanoate
3, 4-dimethyl-2-octene
benzaldehyde
CH 3
H2
C
H3
C
H2
C
C
H2
H2
C
O
C
H2
H2
C
C
C
H2
H2
C
C
H2
CH 3
C
H2
H
C
H3C
O
H2
C
CH
C
CH 3
C
H2
C
H2
O
C
CH 3
H
3, 5-dibromocyclohexanol
2, 4-diiodo-3-hexanone
I
I
OH
CH
H 3C
CH
C
O
Br
Br
2
CH 3
C
H2
4.
Matching: match the compound in COLUMN B with the type of reaction it can undergo
COLUMN A. There may be more than one choice for each reaction. To receive full credit you
need to list all possible compounds for each reaction type.
(20)
COLUMN A
COLUMN B
__C, K_______
hydrolysis
A. 2-methyl-2-butanol
__B, E, I_______
addition
B. butanone
__A, D, F, G, J_
condensation
C. methyl butanoate
___G, A_______
elimination
D. butyl amine
___E, G______
oxidation
E. butanal
___B, E, F____
reduction
F. benzoic acid
___C________
saponification
G. 2-butanol
___D, F______
neutralization
H. methoxy propane
I. 3-hexyne
J. phenol
K. butanamide
5.
For each of the pairs below, provide a simple test that will distinguish between the two
compounds. Indicate what you would expect to see if you performed the test.
(12)
a.
cyclohexanol
and
2-methyl-2-butanol
You can add K2Cr2O7 or KMnO4. The cyclohexanol will be oxidized to cyclohexanone and
there will be a color change from yellow to green or purple to brown. There will be no change
with the tertiary alcohol.
b.
hexanal
and
methyl pentanoate
You can add K2Cr2O7 or KMnO4, Cu2+ or Ag[NH3]+. The hexanal will react positively (yellow
to green, purple to brown, blue to red solid or silver mirror). There should be no reaction with
the ester.
c.
cyclohexene
and
cyclohexane
Add Br2/CCl4 or KMnO4. The cyclohexene will undergo addition and there will be a color
change from orange to colorless or purple to brown,. The cyclohexane will not react.
3
6. a.
For each of pair of compounds below, decide which one is more soluble in water and
explain why.
(8)
propanol
and
propanone
Propanol. It has both a hydrogen on an oxygen and oxygen that can hydrogen bond with
water while propanone has only an oxygen
N, N-diethyl ethanamide
and
N-ethyl butanamide
N-ethyl butanamide. It has a nitrogen and a hydrogen on the nitrogen to hydrogen bond
with water. The disubstituted amide does not have a hydrogen attached to a nitrogen.
b.
Rank the compounds below in order from lowest (1) to highest (4) boiling point and
explain your ranking.
(8)
propanone
propanol
ethyl methyl ether
ethanoic acid
___2______
__3______
____1_____
____4______
While all of these compounds contain oxygen and hydrogen, only ethanoic acid and
propanol can hydrogen bond with molecules of the same compound because one
hydrogen is on oxygen. Ethanoic acid has the most possible interactions. Propanone’s
oxygen is more likely to induce a dipolar interaction than the ether.
7.
H 3C
Complete the following reactions supplying the appropriate product(s) or reactants(s).
(40)
H2 OH H2
H2
H
+
CH
C
C
3
CH 3
C
C
H2O/H
H 3C
C
C
C
C
H2
----------------------->
H2
CH 3
CH 3
H2
C
H 3C
H2
C
CH
OH
C
CH 3
No reaction
O
LiAlH4
----------------------->
O
C
C
H2
Cu2+
----------------------->
OH
CH 3
CH
______________________
C
H2
4
CH 3
O
O
H2
C
C
O
CH 3
C
NaOH
----------------------->
ONa+
H2
C
+
HO
CH 3
HBr
? ---------------Br
OH
H
H2
C
C
O
K2Cr2O7
------------------------->
CH 3
C
H2
O
C
H2
+
H3C
O
O
C
C
O
H2
C
C
C
H2
CH 3
C
H2
O
----------------->
CH 3
C
N
H
NH 2
CH 2
HN
CH 3
O
+
HCl
------------------->
CH 2
-Cl+H 2N
___________________________
5
CH 3
CH3
C
HO
CH 3
6.
BONUS:
For the alkaloid of your choice, provide the following information: (8)
a.
name ____________________________
b.
chemical formula
c.
drug action
6